Synthesis of Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines in Water and their SNAr Cyclizations

被引：12

作者：

Chanu, Langpoklakpam Gellina ^{[1
]}

Singh, Thokchom Prasanta ^{[1
]}

Jang, Yong Ju ^{[2
,3
]}

Yoon, Yong-Jin ^{[2
,3
]}

Singh, Okram Mukherjee ^{[1
]}

Lee, Sang-Gyeong ^{[2
,3
]}

机构：

[1] Manipur Univ, Dept Chem, Imphal 795003, Manipur, India

[2] Gyeongsang Natl Univ, Grad Sch Mol Mat & Nanochem, Dept Chem, Jinju 660701, South Korea

[3] Gyeongsang Natl Univ, Grad Sch Mol Mat & Nanochem, Life Sci Res Inst, Jinju 660701, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2014年 / 35卷 / 04期

关键词：

Tetrahydroimidazo[1,2-a]pyridines; Tetrahy-dropyrido[1,2-a]pyrimidines; Imidazo and pyrido fused [1,8] naphthyridine tetracyclic; One-pot and multicomponent; SOLVENT-FREE; REGIOSELECTIVE SYNTHESIS; BETA-OXODITHIOESTERS; DERIVATIVES; RING; CYCLOCONDENSATION; REACTIVITY; CHEMISTRY; DOMINO; DRUG;

D O I：

10.5012/bkcs.2014.35.4.994

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydropyrido[1,2-a] pyrimidines by a one-pot and three component reaction of alpha-oxoketenedithioacetals, diamines and DMAD in water has been described. Different routes for accessing the desired compounds were examined and a few specially designed-substrates have been utilized further to afford the new imidazo and pyrido fused [1,8] naphthyridine tetracyclic compound by SNAr intramolecular cyclization.

引用

页码：994 / 1000

页数：7

共 34 条

[1]

ALONSOALIJA C, 2003, Patent No. 2003053967

[2] ORAL ANTIALLERGIC ACTIVITY IN ASCARIS HYPERSENSITIVE DOGS - A STUDY OF KNOWN ANTIHISTAMINES AND OF THE NEW COMPOUNDS RAMASTINE (R-57-959) AND LEVOCABASTINE (R-50-547) [J].

AWOUTERS, F ;

VERMEIRE, J ;

SMEYERS, F ;

VERMOTE, P ;

VANBEEK, R ;

NIEMEGEERS, CJE .

DRUG DEVELOPMENT RESEARCH, 1986, 8 (1-4) :95-102

[3] Regioselective Synthesis of Heterocyclic Ketene N,N-, N,O- and N,S-acetals in Aqueous Medium [J].

Chanu, Langpoklakpam Gellina ;

Singh, Okram Mukherjee ;

Jang, Sang Hun ;

Lee, Sang-Gyeong .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (04) :859-862

[4]

Devi LR, 2012, INDIAN J CHEM B, V51, P1426

[5] An efficient transesterification of β-oxodithioesters catalyzed by stannous chloride under solvent-free conditions [J].

Devi, Nepram Sushuma ;

Singh, Sarangthem Joychandra ;

Singh, Okram Mukherjee .

TETRAHEDRON LETTERS, 2013, 54 (11) :1432-1435

[6] An Efficient One-Pot Multicomponent Synthesis of 2,3-Dihydro-3-alkyl/aryl-2-thioxoquinazolin-4(1H)-ones under Solvent-Free Conditions [J].

Devi, Nepram Sushuma ;

Singh, Sarangthem Joychandra ;

Singh, Okram Mukherjee .

SYNLETT, 2012, (14) :2111-2115

[7]

FROHN MJ, 2005, Patent No. 2005070932

[8] Synthesis and antiviral activity of novel erythrofuranosyl imidazo[1,2-a]pyridine C-nucleosides constructed via palladium coupling of iodoimidazo[1,2-a]pyridines and dihydrofuran [J].

Gudmundsson, KS ;

Williams, JD ;

Drach, JC ;

Townsend, LB .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (08) :1449-1455

[9]

GUPTA AK, 1988, SYNTHESIS-STUTTGART, P284

[10] Synthesis, biological evaluation, and molecular modeling studies of new 1,3,4-oxadiazole- and 1,3,4-thiadiazole-substituted 4-oxo-4H-pyrido[1,2-a]pyrimidines as anti-HIV-1 agents [J].

Hajimahdi, Z. ;

Zarghi, A. ;

Zabihollahi, R. ;

Aghasadeghi, M. R. .

MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (05) :2467-2475

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